


The Biggest Regret

by Chelsea072498



Category: SPN, Supernatural
Genre: Angst, Character Death, Death, character resurrection
Language: English
Status: Completed
Published: 2018-06-08
Updated: 2018-06-08
Packaged: 2019-05-19 19:34:31
Rating: Mature
Warnings: Major Character Death, No Archive Warnings Apply
Chapters: 1
Words: 3,387
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14879871
Author URL: https://archiveofourown.org/users/Chelsea072498/pseuds/Chelsea072498
Summary: Reader has always thought of Dean as her greatest disappointment and biggest regret.





	The Biggest Regret

##  **The Biggest Regret**

Dean Winchester was her biggest mistake and her greatest regret.

Y/N watched him drive away with Bobby and Sam. She tried to talk to him but he only shook his head. He pulled her in, kissed her forehead, and then got into the car.

It took her less than fifteen minutes to decide she was through. This time, he wouldn’t be able to smile at her, call her Sweetheart, and use his charms. Dean had been distant for a year and he refused to talk to her when she asked why.

She’d lived with Bobby for seven years. Stepping into her room, her heart ached at the reminders of Dean. An empty storage tub sat in a corner. She grabbed it and started tossing pictures, small mementos from hunting trips together, old flannels, and a blanket. The blanket they laid out on the grass the night they made love for the first time.

Y/N knew that she should put the lid on and stop there for the time being. Her brain said that was all she needed to do. Her heart said otherwise.

She hauled the tub down the stairs and outside. Tears flowed down her cheeks. Every emotion she felt for the last year-longer if she was honest with herself, came to the surface. The pain he caused her time and again. The frustration felt when she tried to get through to him and he shut her out. The anger toward herself for not being strong enough to walk away from him no matter how much he hurt her. Y/N knew this was the only way to rid herself of everything Dean Winchester.

Bobby’s old wood chipper stood like a beacon calling to her. Y/N knew she could put the tub in one of the storage unit. She didn’t have to do this….

If she didn’t, she would eventually haul the tub back upstairs and put everything back exactly where she wanted it. Y/N knew she’d rush outside the next time she heard Baby purr into the driveway.

She didn’t even look as she tossed everything into the wood chipper. She turned it on and waited. She lit a cigarette to pass the time, hoping Dean would come back and catch her. She grabbed a metal trash can and a shovel and scooped up the pieces spit out by the wood chipper. Once the metal trash can was full, Y/N poured lighter fluid over the contents and then lit it on fire.

Y/N watched the fire burn. There was one last thing to do.

Y/N needed to leave this life before it completely destroyed her.

Several hours later, her car was packed and ready to go. Y/N was waiting for Bobby. She owed him more than a note. He took her in after the Winchester’s rescued her years before. Bobby trained her, taught her, and was more of a parent to her than either her mother or father had ever been. Bobby Singer was too important to her to just walk away without a real explanation.

She dozed off waiting for him. Bobby knew when he saw her car loaded up. He would never admit this to anyone, but it was for the best. Especially now.

“Hey,” Bobby gently shook her. “Y/N/N?”

“Hmm?” She slowly opened her eyes and saw him. “Bobby? What time is it?”

“Don’t you worry about that right now.”

Y/N sat up. “Bobby, what’s happened?”

Bobby walked toward the kitchen. “You should go on to your room and get some sleep. We’ll talk later.”

“You look like you could use some sleep but I know you’re about to make a huge breakfast.” She leaned against the door frame. “Bobby, what is it?”

Bobby took a deep breath and turned around. “He’s gone, Y/N. Dean’s….gone.”

Y/N stared at him for several minutes. Bobby sat down at one of the chairs and sobbed. She kneeled in front of him and wrapped her arms around him. “I’m sorry, Bobby. I’m sorry.”

“Hey,” He lifted her face and looked in her eyes. “I’m sorry, Y/N. Dean….he had a tough time showing how he felt about people. I know he loved you in his own way.”

“Dean’s really gone?” Bobby explained Dean’s deal. Y/N closed her eyes. Dean made a deal to save his brother. “Damn him. He should have told me. He could have told me!”

“He thought eventually you’d get fed up and leave. We all suspected one day you’d want out. You got your car packed up so I guess that day came.”

Y/N had to ask. “So why tell me?”

“You fell in love with Dean the moment you met him. You loved him enough not to push him into leaving with you even though we both know that’s what you wanted. You loved Dean enough to know that he’d never put anyone above Sammy or the hunt for the thing that killed his momma.” Bobby sighed. “You’ve got your pictures and your memories…”

“I…” Y/N cried again as she told him about the wood chipper and burning the rest of it. “I was mad and I knew I was making a mistake but I was just so damn….”

“Hey, you got what you had here,” He pointed to her head, “and here.” He pointed to her heart. “He wanted me to tell you to go to Mobile.” Bobby handed her an envelope. “He said there’s some money there for you. He wanted you to start over. He wanted you to move on.”

“Is that really a possibility?” Y/N asked.

Bobby shrugged. “Not for most of us but you’re young. Do this for you, Y/N/N. Do it for Dean. That boy had so many regrets in his life and his biggest regret was that he would never be able to give you the life he knew you deserved.”

She hugged Bobby tight. She loved him dearly but she knew this would be the last time she would see him.

“I love you, Grumpy.”

“I love you, Girl.” Bobby touched her cheek. “You take care of yourself. You do something big with your life. You’ve got some money saved up, Dean left you a little bit. Go out there do something amazing.”

She kissed his cheek. “You can call me.”

Bobby shook his head. “No, Y/N, you’re getting out. You’re staying out.”

As she drove later that evening, Y/N considered turning around and going back to Bobby’s. She was leaving her family behind. That weighed heavily on her as she drove south to the address in mobile. She pulled over and took a few deep breaths. Sam’s phone was off. Bobby would never answer. Ellen would know by now that Dean wanted her out…

“I’ll do it for Dean.” Y/N got back on the road and it to Alabama in record time.

The bank gave her the small lockbox Dean left for her. She already had the key. He gave it to her two years earlier and asked her to hold it for him when he set out to find John. Y/N grabbed a room in town and sat holding the box for several hours before finally opening the box.

She was shocked by the amount of cash in the box. Y/N was even more surprised by the letter she found. As she read Dean’s words, her heart broke all over again. She cried for hours, making herself sick.

Three days later, Y/N was still sick. A crazy idea formed in her head and she managed to shower, dress, and go out for food and a quick stop at the store.

Life changed that night. Y/N found a small, cheap apartment in a small country town. She applied for a job at the local urgent care clinic, putting her nursing degree to use for something other than hunter’s injuries.

Her beautiful baby boy was born in December. Dean’s last gift to her. John Robert Winchester looked exactly like his father. By the time he was two, Y/N knew he’d be exactly like his father.

Y/N was offered a job at Smith County Memorial Hospital in Kansas.  It was a great opportunity for her and she accepted the job immediately. Robbie was excited to go on the adventure and they easily settled into their new life.

On Robbie’s twelfth birthday, he begged to go to the tree lighting ceremony in Lebanon, twenty miles from their home. Y/N hated Lebanon, though she could never explain why. She just knew she never wanted to go into the town.

When she saw her son having fun with his friends from school, Y/N relaxed. Robbie and his friends were throwing snowballs at each other. Y/N laughed when one of the girls got Robbie right in the face. She yelled that she was getting hot chocolate and turned around.

Dean Winchester was standing in front of her.

“Y/N?”

Her smile slowly faded as the color drained from her cheeks. She tried to talk, but no words would come out of her mouth.

“Mom!” Robbie ran over. “Can we go get pizza with Jason and his parents?”

“What?” Y/N looked at him.

“Y/N?” Dean’s deep voice caught the attention of Robbie.

Robbie starred at Dean and then looked at his mother. “Mom, who is this?”

Y/N started to shake. “I…Um…This is..”

“I’m Dean.”

“I’m Robbie. Robbie Winchester.” He extended his hand and Dean was impressed by the strength of his handshake.

Sam approached with a pretty woman with brown hair. He froze and turned to the woman, using sign language to communicate something to her.

“Dean’s a Winchester too.” Y/N managed to get out. Her eyes met Dean’s. “Robbie, I…”

Dean shook his head. “No,” He said.

Sam stepped forward. “Hey, Robbie, right? My name is Sam. This is my friend Eileen. Do you know where they sell the funnel cakes around here? She’s never had one. Eileen’s from Ireland.”

Y/N watched them walk away. She started to follow, but Dean grabbed her arm. “You had my kid?”

“You died and went to hell.” Her voice was low so no one could hear. “I thought you were dead. I tried calling Bobby, and Sam, but they never answered. I don’t know if they even heard my messages. I told them both, through voicemails since no one would take my calls.” She pulled him away from the crowd. She saw several people she knew looking back and forth between father and son. “You were gone. You wrote me that letter and told me to move on. I did. I had no idea I was pregnant until a few days later.”

Dean took a deep breath. “I’m sorry, Y/N. I came back and it wasn’t safe to call you. I got out and I was going to look for you but I thought maybe you’d moved on by then. I didn’t want to show up and possibly ruin your life.” Dean turned and looked at Robbie. The young man was watching him. “He’s not stupid, Y/N/N. He’s our kid.” Dean actually smiled at her.

Y/N smiled back. “I don’t have any pictures of you left so he doesn’t know what you look like.”

“Where’s all our pictures?” Dean asked.

“Don’t ask.” Y/N sighed. “He is smart, Dean. His friends and their parents are here. They aren’t stupid. He’s you.”

Dean bit his lip. “Maybe….could I….”

“You want to officially meet your son?” Y/N asked. “And then maybe explain to me how you came back from Hell?”

“Sammy and I live here in Lebanon. We have for awhile. I don’t know how we haven’t had this happen before.”

Y/N shrugged. “I hate this town. We rarely come over here. I only agreed tonight because it’s Robbie’s birthday and he wanted to see the tree lit up. I promised him burgers and pie at Lenny’s Diner…”

“I love that place.” Dean’s smile was huge. “Can I buy you two dinner?”

“Yeah, if Robbie’s okay with it.”

When asked, Robbie looked at Dean and shook his head. “No.”

“Robbie?”

“I’m not stupid, Mom. I know who this guy is. You have three pictures of him hidden. I found them when I was five.” Robbie looked at Dean. “You didn’t die. You lied to my mom.”

“Baby, it’s more complicated than that.” Y/N looked into her son’s olive colored eyes, his father’s eyes. “Dean went away for awhile and everyone thought he was dead. Dean and I have to have a long talk about a lot of things. He wants to take us to dinner and give the two of you a chance to talk.”

Robbie stared down Dean and shook his head. “No.”

“John Robert!”  
  


“My Mom has cried in her sleep for you. I found her diary.”

Y/N’s eyes widened. “I thought I burned that!”

“I know. I hid it.” Robbie confessed. “I know more than you think, Mom. I know that he hurt you. I know everything.”

Dean kneeled down to his level. “I made a lot of mistakes. I hurt your Mom. That has been my biggest regret until tonight. Now I regret that I didn’t know about you. I regret that I didn’t find Y/N and start a new life with the two of you.”

“It’s too late.” Robbie told him.

Y/N shook her head. “It’s not!” She looked at Dean and then turned to her son. “Baby, you have a chance to get to know your Dad. Had I known he was alive, I would have done anything to make this happen!”

Robbie looked at his mom before moving his eyes to Dean. Dean knew the glare well. He’d seen it in the mirror too many times.

“I don’t need him. I have you.” He looked at Sam. “You’re pretty cool.”

“If you want to talk, you can call me.” Sam offered.

Robbie shook his head. “No, thanks. You’re always going to be on his side. You’ll just try and make me see him.”

Y/N took a deep breath. “You and Dean deserve a chance to talk privately. We’re going to the house and we’ll have an honest conversation…”

“No,” Dean spoke up. “Robbie’s made up his mind, Y/N.”  
  


“He’s a twelve year old kid, Dean.”

Dean gently pulled her aside. “Don’t do this, Sweetheart. Don’t force it.” He took one of the many fake business cards out of his pocket and asked for a pen. He wrote several more phone numbers down, along with an email address. “We can meet up one day and have our conversation if you really want to. I don’t think it’s a good idea if our son doesn’t want anything to do with me.”

“He doesn’t really know what he wants. He’s going off things written in a diary mostly when I was angry….”

“Sam is giving Robbie his number. He’ll be able to get in touch with me if he really wants to.” Dean looked down. “You look good. It looks like you’ve done well for yourself.”

“I just did what you and Bobby asked me to.” Y/N felt tears threatening. “I’ll call you.”

Dean dared to lean in and kiss the top of her head. “I never stopped thinking about you.”

She smiled at their son. “I couldn’t even if I tried.”

He touched her cheek. “I know you. You’ll do what’s best for him. I get it. I will too.”

“Dean…”

“Mom, I’m ready to go.”

Dean looked at his son with a soft smile. He walked over and extended his hand. “Take care of your mother.”

“You can count on that.” Robbie promised.

Y/N looked back several times as they walked away. She gave Dean a small smile and finally walked away without another look back.

“I think the kid may call.” Sam said.

Dean shook his head. “No, he won’t.”

Eileen was watching their lips and asked, “How do you know?”

“He’s my kid.” Dean looked around. “I don’t feel much like being here anymore. You’ve got your car so I’m leaving.”

“Dean?”

“I need some time.”

Y/N finished the pancakes and bacon the next morning just as Robbie walked into the kitchen. “Hey, Mom.”

“Hey, Baby.” Y/N saw he was dressed. “Where are you going at eight on a Saturday morning? I told you we’d go do something today to make up for leaving early last night…”

Robbie shook his head. “Mom, can you call him? Dean…Dad…whatever I’m suppose to call him.”

“Wh…what?” Y/N asked. “What brought this on? Last night you weren’t willing to discuss it at all!”

“I took your tablet and added Sam and Eileen to skype. We talked for awhile. Sam said some things and maybe I should at least hear the guy out.” Robbie shrugged. “I think you have questions too, right?”

“A few.” Y/N put their plates down. “You read about some things I hoped you wouldn’t need to know about. We’ll need to discuss that at some point.”

“Sam and Eileen told me a lot.”

Y/N rolled her eyes. “Okay, do you have any questions?”

Robbie started to say something, but Y/N’s phone rang. “Just a sec. If Jody’s daughter had her baby, I may have to work tonight.” She didn’t recognize the number. “Hello?”

“Y/N?”

“Sam? How did you get my number?” Y/N knew. Robbie gave it to him. She stepped outside her back door for privacy. “Why are you calling so early? Do you want to set up a playdate?”

“Look, something happened last night. I’m at the hospital. I had to come and…” He broke. “Dean was in an accident last night.”

Everything began to spin. “Which hospital?” Y/N asked, almost frantic.

She heard him cry. Sam was struggling to keep himself together. “It doesn’t matter. I’m taking him back to the bunker…our home. I wanted you and Robbie to know. If you want to be there…”

“He’s gone?” Y/N asked. “Dean’s….I’ve been through this before, Sam. I still don’t know what happened..”

“I’ll tell you everything. This time, Dean’s not coming back.”

Y/N saw her son nibbling on bacon. “Robbie asked me to call him. He said…” She felt the tears falling down her cheeks. “I wasn’t stupid enough to think Dean and I could pick back up after all these years, but my son could have had a chance to know him. I think he wanted that chance….What’s your address? We’re coming.”

“Y/N, are you sure?”

“Yes.” Y/N took a deep breath. “I didn’t get a chance to say goodbye last time. I have a lot of regrets, Sam, and that was one. I didn’t get a chance to tell Dean goodbye. I don’t want to have that regret. Robbie’s going to have regrets. He’s going to kick himself for not agreeing to talk to Dean last night. We need to be there. There’s been too many disappointments, too many regrets already. This won’t change things or bring Dean back, but it’s what we need.”

“It’s what Dean would want.”

Y/N watched the flames. Robbie was silent. She knew everything would hit him hard later. She reached over and touched his shoulder. He turned and rushed into her arms.

Eventually, Eileen suggested they all go inside. Sam hesitated but Eileen took his hand and pulled him away. Robbie started to follow, but stopped.

“Mom?”

“Go on. Someone needs to keep an eye on this.” She told him. “It’s okay. It’s not the first Hunter’s funeral I’ve been to.” Y/N kissed the top of his head. “Go inside with Sam and Eileen. I’ll be there soon.”

Y/N stared at the fire. Dean Winchester was her biggest disappointment and her greatest regret. She knew things were going to get more complicated now that Robbie acknowledged that he knew the truth. Y/N was now going to be tasked with keeping her son away from a life that broke and destroyed everyone who wandered into it.


End file.
